Brief intro: have cycled to work nearly all of my career, 30-some years. Here in New England that's challenging; if there's too much snow or ice I walked to work, about 2.5 miles through the woods and under the power lines (and a few back yards). Now I've got DSL and mostly work from home, less reason to go out. But I ride as much as I can, did 17 miles & good hills yesterday.
Never took more than 2 or 3 weeks off vacation, but Intel has a sabbatical policy: after 7 years, everyone gets 8 weeks off. Mine is coming up in about 3 months.
Meanwhile, I drive my parents' car twice a year between Florida & the Bershires cabin here in MA, have done that for 3 trips now... and the next one comes up in about 3 months. Normally I get cheap airline tickets, fly one way drive back. This time ... why not do it under my own power?
It's a scary proposition, but this may be the best / only chance to do an adventure like this, before I retire. I keep in shape, do a few centuries or equivalent every year ... but riding 60 to 100 miles a day for 3 weeks is different and a heckuva lot more challenging I'm sure. Will my body hold up? I've been reading the "Touring" forum and will go there next.
Basically I'm asking a lot of questions about finding the best route - fairly direct and fast, if possible, but not suicide roads. I know about Adventure Cycling, looked at their route and wondered if shorter (but save) routes exist.